Preparative Organic Chemistry
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ChemInform Abstract: Conversion of Olefins to Ditriflates by μ-Oxobis((trifluoromethanesulfonato)(phenyl)iodine).
First published: January 12, 1988
Abstract
Triflic anhydride (I) inserts 2 equiv. of iodosobenzene (II) to form Zefirov's reagent (III) which undergoes addition reaction with ethylene (IVa), propylene (IVb), and cyclohexene (VI), producing the 1,2-ditriflates (V) or (VII).
ChemInform Abstract
Triflic anhydride (I) inserts 2 equiv. of iodosobenzene (II) to form Zefirov's reagent (III) which undergoes addition reaction with ethylene (IVa), propylene (IVb), and cyclohexene (VI), producing the 1,2-ditriflates (V) or (VII). Butadiene (VIII) and (III) yield a 89:11 mixture of 1,4:1,2 adducts which are converted to E-1,4-dibromo-2-butene (X) on treatment with tetraethylammonium bromide (IX).The reaction of (III) with cis- and trans-1,2-dideuteroethylene is also investigated.
